Diethylamine → HCID 44540958, compound

HRID 1616015Notes

Reaction equation

HRID 1616015 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][NH:24]4)[CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][NH:15]3)=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH2:29]([NH:31][CH2:32][CH3:33])[CH3:30].CCN(C(C)C)C(C)C>CS(C)=O.CS(C)=O.CO>[CH2:29]([N:31]([CH2:32][CH3:33])[C:2]1[N:7]=[C:6]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][NH:24]4)[CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][NH:15]3)=[O:9])[CH:5]=[CH:4][CH:3]=1)[CH3:30]

Participants

6

Reactant 3

HCID 8021Diethylamine4×HCID 81531Diisopropylethylamine2×HCID 44540963HCID 44540963, compound

Product 1

HCID 44540958HCID 44540958, compoundYield 4.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 22036561Dimethyl sulfoxide methanolSolvent

Conditions

Temperature
160 °C

Procedure

To a microwave vial was added 2 ml of a solution of 6-chloro-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide (350 mg, 0.90 mmol, prepared as described in Example 18) in DMSO (14 ml). Diethylamine (0.027 ml, 0.26 mmol) and DIPEA (0.113 ml) were added and the mixture was heated at 160° C. for 2 h under microwave irradiation. Further diethylamine (0.027 ml, 0.26 mmol) was added and the mixture was heated at 160° C. for 2 h under microwave irradiation. Again, diethylamine (0.027 ml, 0.26 mmol) was added and the mixture was heated at 160° C. for 1 h under microwave irradiation. After this time, diethylamine (0.027 ml, 0.26 mmol) and DIPEA (0.113 ml) were both added to the mixture and it was heated at 160° C. for 2 h under microwave irradiation. The crude reaction mixture was dissolved in DMSO/MeOH (1:1) and purified by Mass Directed Automated Preparative HPLC (Method E). Product-containing fractions were dried under a stream of nitrogen to afford the title compound (4.7 mg).

Workup

  1. temperaturethe mixture was heated at 160° C. for 2 h under microwave irradiation
  2. temperaturethe mixture was heated at 160° C. for 1 h under microwave irradiation
  3. additionboth added to the mixture and it
  4. temperaturewas heated at 160° C. for 2 h under microwave irradiation
  5. customThe crude reaction mixture
  6. custompurified by Mass Directed Automated Preparative HPLC (Method E)
  7. customProduct-containing fractions were dried under a stream of nitrogen

Sources & evidence

ORD record
ord-3e03c2dd9dd44646a0882157a23393e3
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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